My Very Worst Date

After much encouragement to try an online dating service, I decided to go the el cheapo route and signed up for Plenty of Fish. My inbox was immediately bombarded with messages, most consisting of one or two incoherent sentences. One gentleman caller stood out from the rest, and after communicating for a few months, I drove from Washington DC to Richmond to meet him in real life.

I followed his driving directions, but upon arriving at my final destination, I realized I was outside of a halfway house. He was standing there with a backpack. He looked the same as his pictures until he smiled. Both of his front teeth were missing.

I tried to make do by going to a public place with this guy to kill some time before I could exit gracefully. We went to a bar where he talked of his sobriety and pounded Red Bulls.

He was interrupted by a tall, lanky, transient-looking man who asked, “Hey man wasn’t I locked up with you?”

After catching up for a few minutes, his inmate friend left and my date filled me in on the fact that he had gone to prison in his “past” (read: recently released) for narcotics trafficking and assault with malicious intent.

We never saw each other again, but he called my phone at least once every few months for five years, to leave a message that I’m “always in heart and mind.” Our date was seven years ago.

(originally printed on My Very Worst Date in 2009. And guess what? I made the BEST OF page.)

Wow freaky stuff, I make a habit of blocking people like that from calling me as soon as possible.

I have had more than a few unpleasant surprises from people I have met internet dating, including one time where on a first date she wanted me to help steal a car she had her name on, but had never driven or paid for from her ex boyfriend. In fear that she might do the same to me one day, I just said no and walked away.